Hydrochloric Acid → HCID 58557188, compound

HRID 1969661Notes

Reaction equation

HRID 1969661 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C:9]2[N:13]3[C:14]4[CH:20]=[CH:19][NH:18][C:15]=4[N:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[C@H:6]([CH2:21][CH3:22])[CH2:5]1)=[N+]=[N-].BrCC(OC(C)(C)C)=O.Cl.N([C@@H]1CN[C@H](C)C1)=[N+]=[N-].N([C@@H]1CN(C(OC(C)(C)C)=O)[C@H](C)C1)=[N+]=[N-].[OH-].[Na+].[H][H]>CCO.[OH-].[OH-].[Pd+2]>[CH2:21]([C@H:6]1[N:7]([C:9]2[N:13]3[C:14]4[CH:20]=[CH:19][NH:18][C:15]=4[N:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[CH2:8][C@@H:4]([NH2:1])[CH2:5]1)[CH3:22]

Participants

10

Reactant 7

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 140411971,1-Dimethylethyl (2R,4S)-4-azido-2-methyl-1-pyrrolidinecarboxylateHCID 58558006HCID 58558006, compoundHCID 86660442HCID 86660442, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58557188HCID 58557188, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To the solution of 8-((2R,4S)-4-azido-2-ethylpyrrolidin-1-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.136 g, 0.459 mmol, prepared using S from Example #3 Step E and tert-butyl bromoacetate, E with HCl, H with (2R,4S)-4-azido-2-methylpyrrolidine (prepared from (2R,4S)-tert-butyl 4-azido-2-methylpyrrolidine-1-carboxylate as detailed in Rosen, T.; Chu, D. T. W.; Lico, I. M.; Fernandes, P. B.; Marsh, K.; Shen, L.; Cepa, V. G.; Pernet, A. G. J. Med. Chem. 1988, 31, 1598-1611, then E with HCl), OO, D with NaOH) in EtOH (15 mL), 20% palladium hydroxide on carbon (0.05 g, 0.071 mmol) was added and the reaction mixture was stirred under atmospheric pressure of hydrogen for 2 h. The catalyst was removed by filtration through a pad of Celite® and the solvent was removed under reduced pressure to yield (3S,5R)-5-ethyl-1-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)pyrrolidin-3-amine (0.11 g, 89%) as an off-white amorphous solid. LC/MS (Table 1, Method a) Rt=1.00 min; MS m/z 271 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite®
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cd3a50797a2f4769a8610f2603262fab
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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